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- Season 5 overviewOct 18, 2000-May 23, 200123 episodesSeason 5 episodes1. Hello Charlie Oct 18, 2000
- Charlie is late to his own press conference announcing his position as the new deputy mayor.
- 2. Smile Oct 25, 2000
- Charlie needs to find a new dentist before a photo shoot; Caitlin hires a new assistant.
- 3. The Spanish Prisoner Nov 1, 2000
- Havoc ensues when Caitlin reveals to the press that Charlie is enrolled in a Spanish class.
- 4. The Bone Collectors Nov 8, 2000
- Caitlin is a guest on "Live With Regis"; a construction crew finds bones underneath the highway.
- 5. Blind Faith Nov 15, 2000
- Caitlin decides to work on her personality after a blind man breaks up with her.
- 6. Balloons Over Broadway Nov 22, 2000
- Paul pretends Caitlin is his girlfriend when his mother makes a surprise visit.
- 7. Lost and Found Nov 29, 2000
- Charlie and Caitlin compete for Sam's (Rena Sofer) attention.
- 8. All the Wrong Moves Dec 6, 2000
- Charlie crushes the mayor's ego when he wins a racquetball match.
- 9. The Burgers of Wrath Dec 13, 2000
- The mayor and staff spend time working in a fast-food restaurant.
- 10. Toy Story Dec 20, 2000
- The mayor hopes to bag a great Christmas photo-op; Carter and Caitlin help out at a retirement home.
- 11. The Perfect Dorm Jan 10, 2001
- Paul tries to get over his ex-wife by moving into a college dormitory.
- 12. Hey Judith Jan 17, 2001
- The mayor's new girlfriend becomes involved in policy issues.
- 13. The Gambler Jan 24, 2001
- Charlie joins Paul and Carter's poker nights and relapses into gambling.
- 14. In the Company of Dudes Feb 7, 2001
- Charlie calls on a college buddy to represent the mayor in a lawsuit.
- 15. The Image Maker Feb 14, 2001
- Caitlin hires an image consultant to determine why the mayor's approval rating with women is down.
- 16. Trainstopping Feb 21, 2001
- The press has a field day when the mayor parks his limo in a children's van-pool spot.
- 17. Rain on My Charades Feb 28, 2001
- The mayor asks Caitlin for help when his daughter's lifestyle becomes a bit much.
- 18. You've Got Male Apr 25, 2001
- Caitlin poses as "one of the boys" to compete with Charlie for an important account.
- 19. Minor League May 2, 2001
- Charlie attempts to relive his past by trying out for a minor league baseball team.
- 20. Science Friction May 9, 2001
- Caitlin falls for a sexy philanthropist; Charlie temporarily takes over as acting mayor.
- 21. Brotherly Love May 16, 2001
- Charlie and Tim try to impress Caitlin; Stuart and Paul mistake Carter's sister as his lover.
- 22. A Shot in the Dark May 23, 2001
- When a gun shot lands Charlie in the hospital, he uses his condition to milk Caitlin for attention.
- 23. A Shot in the Dark May 23, 2001
- When a gun shot lands Charlie in the hospital, he uses his condition to milk Caitlin for attention.